What is it like to be a female CEO in Silicon Valley? originally appeared on Quora - the knowledge sharing network where compelling questions are answered by people with unique insights.
Overall, a positive experience. I've been fortunate to not have any specific serious issues, and I've been extremely lucky in the caliber of people and teams I have around me. I do hear unfortunate stories from others -- they exist -- but my personal one has been one of growth and challenges.
My experience as co-founder and CEO at Lever (we're a B2B SaaS company building collaborative recruiting software) has very much evolved in distinct stages as we've grown as a company -- in other words, being a female CEO feels different at Seed vs Series A vs Series B.
Seed stage - it all comes down to the people
Back when we were a small company, less than 10 people, I was the only woman at Lever for 1.5 years and benefitted quite a lot from the intimacy of the team. I was lucky to be on a team where everyone respected each other and had solid communication skills and self-awareness. Gender didn't feel like a prevailing factor, and my skills as a designer/developer were critical to success. But I've heard many horror stories about this stage from others because it literally comes down to the people. I was lucky; some aren't, and at this early stage, peoples' personalities and communication styles largely govern how decisions are made and what culture is formed.
Series A - the "Mom" stage
When we grew past 10 or so people, we were just starting to sell our product, onboard new users, hire new teammates. Our work was getting more complex. There was a lot of work to be done that was nobody's job; and in particular, a lot of organization, communication, and operational work. For a while, I fell into a pattern of running around, handling as much as I possibly could on top of my "normal" workload, cajoling/nagging people to do what I asked, to share the load. Eventually, I noticed other women on the team similarly picking up a lot of the slack and chores. It wasn't just a CEO thing; it was playing out in the broader team.
Once we noticed it, we changed it. The whole team -- men included -- was receptive to hearing about the situation and generating ideas to fix it. Around the same time, we started our first D&I committee and started talking more intentionally about our culture.
I must admit -- that transition was somewhat hard for me. I had to claw myself back to strategy, recalibrate the value of my time, and more formally delegate. It felt foreign and "authoritarian" to me at first, it's not my natural leadership style. But probably the big insight I had at this stage was that Lever didn't need someone to support them; it needed someone to challenge them.
Series B - everyone notices you're a female CEO
Funnily, I didn't think much about being female in Silicon Valley until I became a CEO. And I didn't think about being a female CEO in Silicon Valley until we hit 50 employees. That was about six months ago (Lever is 85 employees today), so I'm still watching this one play out.
I'm noticing that in this phase, the biggest change is that in addition to be ing a strategic leader -- on product, fundraising, etc -- I'm now becoming a cultural leader. I get many more questions nowadays about "what it's like" and career advice for women in tech. More invites to be on speaking panels, more invites to women leadership groups. Perhaps most startling, people are joining our company *because they want to work under a female CEO.* Wow.
It seems that there's more perceived symbolism than I have encountered so far. And it's making me make a lot more choices of whether or not I'm "gendering" some of my actions. When we hit a rough patch, do I respond with "objective reality" or "nurturing encouragement"? Do I support us prioritizing the hiring of more women into sr/management roles, even if it means delaying the search? Should we reduce outright competition among/within teams because that's could be perceived as un-inclusive?
Though I'm just speculating here, I'm probably spending more time thinking about how my actions are perceived/read by others more than a male counterpart would.
Fundraising - deserves its own section
The sharpest self-awareness I have as a female CEO comes when fundraising. That's generally when I notice that I literally am the only woman in the room. I should note that I've never had any bad experiences with any specific VCs; it's just the patterns and prevalences of the system overall.
In general, raising money does truly feel like I have to act differently from who I am in order to succeed. You need to be more confident, more aggressive, more assertive -- traditionally "male" attributes -- all in order to "pattern match" to previous successes to decrease the risk of the investment. Well, as a female CEO, you're not going to pattern match to the majority of past successes. Especially if you're building a company that's not geared specifically towards female users.
Fundraising is so important to Lever, to our employees, to everything we've invested so far, that *I* don't take risks either. I bring my tall, white, male, technical, ex-Google co-founder, Nate, to fundraise with me -- just in case people have that unconscious need for the security of the familiar. Nate is amazing, talented, and incredibly supportive of me; we joke about the absurdity of it all while driving up and down Hwy 280 together. I'm appreciative of him and every other person at Lever for having my back.